


Stiles Shouldn't Assume

by machtaholic (cinderella81)



Category: Teen Wolf (TV)
Genre: Alternate Universe, Bottom Stiles Stilinski, Crack, First Time, M/M, Top Derek
Language: English
Status: Completed
Published: 2013-09-08
Updated: 2013-09-08
Packaged: 2017-12-25 22:59:56
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,654
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/958623
Author URL: https://archiveofourown.org/users/cinderella81/pseuds/machtaholic
Summary: <blockquote class="userstuff">
              <p>This came from MajaLi over on Tumblr:  Stiles thinks Derek is a gay hooker who lives in his apartment building (like maybe he sees this constant parade of dudes and overhears money talk that out of context makes it seem they're customers, not one night stands?) but what the hell, Derek is hot & nice so Stiles makes friends BUT THEN DEREK'S SUPER AWKWARD FAILWOLFY attempts at boyfriending/sexytimes? :D :D </p><p>This turned into ... Stiles thinks Derek is a hooker, but it turns out Derek is a ... wait for it ... hair stylist!  Stiles goes to apologize and gets coerced into a dinner date and a haircut which leads to ... sex, of course!  I've been told that this is more than fandom crack, it's fandom meth ...</p>
            </blockquote>





	Stiles Shouldn't Assume

**Author's Note:**

  * For [MajaLi](https://archiveofourown.org/users/MajaLi/gifts).



When Stiles looked back, it still made sense to him. The comings and goings at all hours of the day, and sometimes late at night - men, women, even couples! Being that Stiles lived on the same floor and saw them either coming, or going, it was obvious - Derek Hale was clearly a hooker. Anytime he saw someone leaving, they were passing Derek some bills, which he’d shove into the pocket of his sinfully tight jeans.

It all went to hell when he came home from grocery shopping to find Scott, his _married_ best friend waiting outside Derek’s door.

“Dude,” Stiles said. “Dude … tell me you’re not doing this. You couldn’t have come to me first?”

Scott blinked and turned to Stiles. “Why would I come to you? Allison set this up for me,” he said, looking confused.

“Allison set … okay,” Stiles said, fumbling with his keys and his groceries. “Dude.”

Derek’s door opened and he stepped out into the hallway. Stiles tried not to stare at the man, barefoot in a pair of dark wash jeans and a white wife beater. “Scott McCall?” Derek’s voice rumbled through the hallway.

“That’s me,” Scott said with a grin.

“Come on in, I have another appointment in an hour,” Derek stepped back into his apartment and motioned for Scott to follow.

“Wait, Scott, man,” Stiles said. “Can we talk about this?”

“I’ll come see you when I’m done, man,” Scott said, giving Stiles a wave before closing Derek’s door.

“Fuck,” Stiles said, rushing into his apartment and putting his groceries on the kitchen counter. His mind raced as he put his stuff away, trying to wrap his brain around everything. Did Allison set it up so Scott could experience some weird werewolf sex? It was obvious that Derek Hale was a werewolf - not just because he was unnaturally attractive, but his name had that little ‘w’ next to it on the buzzer chart outside their apartment building. It didn’t bug Stiles, because hey, his best friend had been bitten by a werewolf and had to register, too. But … why hadn’t Scott come to him first? Stiles would have helped research some alternatives besides Derek Hale.

Stiles lost track of time and fell off the couch when he heard a knock on the door. He pulled the door open and tugged his best friend into his apartment. “Scott, dude, talk to me,” he said. “What is going on? What were you think … “ Stiles stopped and stared at his friend. “Did you get a haircut? Seriously? You got a haircut before talking to me?”

Scott blinked at his friend. “Well, yeah,” he said slowly. “Allison made the … Dude, Stiles, you research and get information on everyone. You knew everything about Mrs. Metlzer two days after she moved in two floors down and you didn’t research your neighbor down the hall?”

“Um … no,” Stiles admitted. “I was a bit distracted by the werewolf-ness and ridiculous hotness of my new neighbor.” He shoved his hands in his pockets and looked a bit sheepish.

“Stiles,” Scott said, rubbing his face. “Your neighbor, Derek Hale … is a hair stylist.”

“A what?”

“A hair stylist,” Scott said, rubbing his nape. “He’s apparently, like, the best in Beacon Hills, but you only get an appointment if you know someone who’s his client. He doesn’t advertise, it’s all word of mouth.”

“Well fuck,” Stiles said, running a hand through his hair. “I feel like a dick.”

“You of all people know better than to assume things,” Scott said. “You are the king of conclusion jumping.”

“Sometimes I’m right,” Stiles said halfheartedly.

“And sometimes you’re not,” Scott said. “Listen, Allison’s making lasagna tomorrow night … come over for dinner?”

“Yeah, sure,” Stiles said, clapping Scott on the shoulder. “Sorry … about the conclusion jumping.”

“Uh-huh,” Scott said. “See you tomorrow.”

When Scott was gone, Stiles plopped down on the couch and sighed. “I should go apologize,” he said. “But … he doesn’t know I thought he was a hooker. I still feel bad, though. I should go apologize.” He sighed again and launched himself off the couch, shoved his keys in his pocket and headed down the hall.

He took a couple of breaths before knocking on Derek’s door. The door opened and instead of Derek was … Lydia Martin, who brushed past him with a ‘bye Stiles’, her heels clicking on the hallway floor.

“Stiles, right?” Derek stood in the doorway, eyeing Stiles.

“Um … yeah, me, Stiles is … me.” Stiles sighed and rubbed his face. “I wanted to stop by and … apologize.”

“For what?” Derek asked.

“Well,” Stiles ran a hand through his hair and had the decency to look embarrassed. “I made some assumptions, about you … and I was wrong, and I wanted to apologize.”

“Apologize for what?” Derek motioned for Stiles to followed him inside. “Coffee? I don’t have any appointments for the rest of the day so … “

Stiles hesitantly stepped inside, glancing around the apartment. It was Spartan, but comfortable. Near the window was a small salon set up, complete with a red leather barber chair. “Sure, coffee,” Stiles said softly. “Um … I didn’t know you were a … stylist.”

“I don’t advertise,” Derek said, pouring two cups of coffee. “I have a big inheritance and I don’t really need to work, but … I’d be bored otherwise. I went to the Aveda Institute for Cosmetology, then to the Atlas Barber School before doing a three year stint at Astor Place.”

“Wow, impressive. Um … I thought you were a … hooker.” There, Stiles had said it.

Derek spat his coffee out and coughed. “A … a what?” he said between coughs.

“Hooker,” Stiles repeated. “You had all these people coming and going and they pay you in cash and you’re a werewolf and ridiculously attractive and -”

“You didn’t realize that they looked just a little different when they left?” Derek asked, chuckling softly.

“I only saw them either coming, or going,” Stiles admitted. “I don’t know why I didn’t just come and talk to you that day you were moving in … I’ve been told I’m very nosy.” He looked down at his coffee for a minute. “I shouldn’t have assumed and I’m sorry.”

“Apology accepted on two conditions,” Derek said, his eyes twinkling mischievously.

“Two conditions?” Stiles queried. It freaked him out just a little that Derek was being so good about it all.

“One, dinner,” Derek said.

“I can’t really cook, but I can attempt … or there’s always takeout,” Stiles said.

“No,” Derek said. “We go out to dinner. Maggiano’s down on Fifth.”

“That’s totally a date place,” Stile said. “Do you want to take me out on a date? Because if so, sign me up! I mean, look at you - tall, dark, very handsome. And … you’re a good sport about this misunderstanding thing, so …”

“Do you always do that? Just keep talking with no filter?” Derek asked, brows furrowed.

“Kind of a habit I never learned to break, sorry,” Stiles said with a shrug.

“Then I’ll take your verbal stream of consciousness as a yes,“ Derek said with a smile. “Second condition, you sit in that chair.” He pointed to the red barber chair near the window.

Stiles swallowed and looked back at Derek. “There. You want me to sit there?” he asked.

“Yep,” Derek said. “Those are my two conditions - you sit for me and we go out to dinner.”

Stiles was quiet for a few minutes, then chuckled softly. “You could have just asked me out, you know,” he said. “Kinda fail at the whole social skills thing?”

Derek shrugged. “My sister called me socially retarded,” he said. “A habit I never learned to break.”

Stiles grinned. “Touche,” he said. “And sitting there?”

Derek shrugged again. “I’ve actually been itching to get my hands on it since I moved in,” he said. “You grew it out recently, right?”

Stiles ran a hand through his hair. “Yeah, was sporting a buzz cut, then I grew it out, got sick of it and cut it again and now I’m growing it out. Almost want to just buzz it down again -”

“Don’t,” Derek interrupted. “Sit for me and you won’t want to buzz it.”

“O … kay,” Stiles said, cheeks a bit pink. “You do know this is very weird, right?”

“What?” Derek asked.

“This whole thing, me going out on a date with you and letting you cut my hair just so you’ll forgive me for me thinking you were a hooker,” Stiles said. “It’s weird.”

“As you said, I kind of fail at social skills,” Derek said. “You provided the perfect opportunity for me to blackmail you.”

“It is a bit of blackmail,” Stiles said. “But … you’re epically hot so … it’s okay.”

“I’m going to let you know right now that … I’m not good at this,” Derek said.

“Being social?” Stiles asked. “I’m quickly figuring that out. But I’m willing to risk it. And hey, if it fails, then I have a new friend and a new stylist, right?”

“Right.”

* * *

It took them a while to actually go for dinner, during which time Stiles and Derek excelled at the flirting, but failed at the small talk. Derek was right when he said he failed at social skills … their small talk was miniscule. The first hour of their dinner, when they eventually made it to dinner, was painful.

They did talk a little about work - Stiles talked about how much he loved his job. He and one of his good friends Danny actually got paid to hack companies computer systems and test their security. He got to work at home, and could work in his underwear if he wanted to.

“Work in your underwear, huh?” Derek said, sipping his wine.

Stiles shrugged and ate a breadstick. “It’s an option I have,” he said.

“I don’t really have that option, even though I work from home, too,” Derek said.

“Oh, I don’t know.” Stiles sipped his wine and eyed Derek with a mischievous grin. “I’m sure your customers would enjoy it.”

Derek snorted and downed the rest of his wine. “I’m sure some would,” he agreed. “I’m a bit old fashioned, though, I don’t go showing the goods to just anyone.”

“Showing the … “ Stiles burst out laughing, dropping his fork into his food. “Old fashioned is right!” He wiped his hands on his napkin and gave Derek a bright smile. “I don’t let just anyone see what’s under this awesome Green Lantern t-shirt.”

Derek chuckled and dropped his napkin on his plate. “The first condition has been met and you are one step closer to forgiveness,” he said with a smile.

“But dessert,” Stiles complained.

“I have double dark chocolate fudge brownies in my apartment,” Derek replied. “Homemade.”

“Double dark chocolate fudge?” Stiles did not whimper. Nope.

Derek nodded and gave Stiles a seductive smile. “Mmmhmm,” he hummed. “And if you’re good when you sit for me … I’ll let you have two.”

“I can be good,” Stiles whispered.

“I bet you can,” Derek said, dropping some bills on the table to cover the tab. “Come on, time to fulfill that second condition.”

“Fine,” Stiles muttered, standing and following Derek out to the Camaro in the parking lot. “I love your car.”

“So you said on the drive over,” Derek said, holding the passenger door open for Stiles, who slid in with only minimal flailing.

Stiles’ nerves kicked back in once he was inside Derek’s apartment. He hesitated near the front door, watching as Derek kicked off his shoes and tugged off his socks, padding around the living room barefoot, turning on lights. “Brownies?” Stiles asked, still near the front door.

Derek tugged his sweater off, leaving him in just a wife beater which hugged and accentuated every muscle. “You want one now?” Derek said. “Or after … “

Stiles swallowed and shrugged out of his coat, hanging it near the door. “Maybe after,” he said. “Don’t think I could eat anything else right now. Nerves.”

“What do you have to be nervous about? It’s just a haircut,” Derek said, flipping on the lights around the barber chair. “Take off your shoes and come sit.”

Stiles tugged his shoes and socks off and padded across the living room, slowly settling in the barber chair. It was … comfortable. The leather almost seemed to wrap around him and it made him feel safe. “I haven’t sat in a chair like this in a long time,” Stiles admitted. “Been cutting my hair myself since middle school.”

“Any reason?” Derek asked gently.

“It’s cheaper and easier,” Stiles said, trying not to flinch as Derek eased him back and wrapped the cape around him.

“I get that,” Derek said, running his hands through Stiles’ hair. “There’s just something about letting someone else do it for you, though.”

Stiles hummed softly, enjoying the feel of Derek’s hands in his hair. “Guess,” he mumbled.

“Your hair’s too long,” Derek commented softly, taking a moment to spray Stiles’ hair with water and combing it back. “That’s part of the reason you’re not happy with it.”

“Is that so?” Stiles replied, watching Derek in the mirror. Derek’s arm muscles would flex and move under his skin as he moved around the chair. “So my idea of just buzzing it again would have worked.”

Derek rolled his eyes and snatched a pair of scissors off the cart. “No,” he said. “That is the easy way out. A buzz cut is not a style.” He moved quickly, combing and snipping, combing and snipping, dropping locks of hair on the ground around Stiles.

“Sure it is,” Stiles said. “It’s the ‘I don’t have money’ style.”

“I’m sure hacking security systems for big companies pays quite a bit,” Derek replied, running his hands through Stiles’ hair, making sure the cut was even.

“I do all right,” Stiles said, trying not to shiver at the feel of Derek’s fingers in his hair. It seemed like Derek’s hands knew just where all his tense spots were and the fingers would rub gently, releasing the pressure.

“I’m sure,” Derek murmured, brushing stray hairs away with a little brush. “Now, this is a style.” He removed the cape from Stiles and blew a bit of hair off Stiles’ neck.

Stiles shivered and bit his lip, eyeing his reflection. Derek did good work, he couldn’t deny that. Shorter along the back and sides, longer on top, styled up and away from his face … “I look good,” he declared. “But … I think you missed a bit of stray hair.” He pointed to a spot just below his ear. “Right here.”

“Right there?” Derek said, his eyes dark as he leaned down and blew warm air at the spot Stiles had pointed to. “Did I get it?” he whispered in Stiles’ ear.

“Th-think so,” Stiles stuttered. “But … I think it slipped under my shirt.”

“Maybe you should take your shirt off,” Derek breathed.

“Take off my shirt?” Stiles stood and faced Derek, his eyes twinkling. “Why Mr. Hale, we haven’t even kissed!”

Derek growled and pulled Stiles close, pressing his lips Stiles’ in a possessive, bruising kiss. His hands slipped under Stiles’ shirt, his fingers exploring the warm skin he discovered.

“Now we’ve kissed,” Derek hummed as he broke the kiss. “Now take your damn shirt off.”

“Am I forgiven then?” Stiles teased. “For thinking you were a hooker?”

“The two conditions have been met.” Derek reached for the hem of Stiles’ shirt and tugged it over Stiles’ head, tossing it aside.

“I could have done that myself, had you just had a little more patience,” Stiles teased.

“No patience,” Derek growled leaning in and sucking a spot on Stiles’ shoulder. “Bedroom.”

“But what about brownies?” Stiles couldn’t help but tease Derek just a little. “I was good, don’t I get two double dark chocolate fudge brownies?”

“Later.” Derek nipped at Stiles’ shoulder and urged him towards the bedroom. “The past couple of weeks have been torture. The flirting, the smiles, the innuendo.”

“I’m very good at flirting,” Stiles said, letting Derek herd him towards the bedroom. “Better than you are at small talk.”

“As we have previously discussed, I fail at social skills.” Derek turned on a light in the bedroom before tugging his wife beater off and tossing it towards the hamper.

“Don’t you think this moving a little fast?” Stiles asked as he undid his jeans and shoved them down, stepping out of them and kicking them aside.

“I consider the past few weeks foreplay,” Derek replied as he tugged off his own jeans, revealing his choice to go commando.

Stiles swallowed at the sight of a very naked Derek Hale. “Oh,” he whispered, licking his lips. “Foreplay?”

Derek nodded, closing the space between them. He leaned in and kissed Stiles again, this time gently, his lips almost caressing Stiles’. His hands trailed down Stiles’ shoulders, arms, around his waist and under Stiles’ boxers. “You should take these off,” Derek murmured, slowly pushing the boxers down.

“Yeah,” Stiles said softly, letting Derek rid him of his boxers. He stepped out of them and leaned against Derek, nuzzling Derek’s neck almost shyly. He should have been worried that they were moving too fast, that this was only their first date and they were already climbing into bed … but he wasn’t.

Derek’s hand moved up Stiles’ back to his hair, tugging playfully. “Bed, Stiles,” he hummed, urging them forward until they toppled onto Derek’s very large bed.

Stiles did not squeal as he flopped back onto the bed, shifting so he was in the center of Derek’s bed. “Sturdy bed,” he commented with a smile.

“Has to be,” Derek replied as he crawled up the bed, covering Stiles’ body with his own. “Has to be. Werewolf, remember?”

“How could I forget?” Stiles said, running his hands over Derek’s chest and abs. “Graceful, quick reflexes, unnaturally hot … “ He gave a little grunt as Derek tugged at his hair again, feeling a tingle shoot down his spine and settle in his groin.

Derek grinned and tugged again, watching the desire and want burning in Stiles’ eyes. “I found a kink,” he purred, suckling at Stiles’ jaw.

“No visible marks,” Stiles whimpered, wiggling under Derek’s assault. “Seeing … seeing my dad tomorrow for dinner … “

Derek hummed and shifted down, latching onto one of Stiles’ nipples, grinning when he heard Stiles keening softly.

“Fucking … shit,” Stiles groaned, scratching his nails down Derek’s back. “You need to be fucking me … now.”

“I think I can oblige you,” Derek said, releasing Stiles’ nipple. He reached over and snatched a bottle of lube and a condom from the bedside table. He coated two fingers in lube and carefully slipped them into Stiles, thrusting gently.

“Just … happen to … keep lube and condoms nearby?” Stiles said as he spread his legs wider and arching off the bed; Derek’s fingers were doing wonderful things.

Derek smiled and pressed a kiss to Stiles’ collarbone. “The lube is for friction,” he said. “Werewolves move faster than humans … “ He cautiously added a third finger inside Stiles, watching him carefully. He was pleased when Stiles merely spread his legs further and gave a delicious little whimper.

“And the condoms?” Stiles gasped.

“Got them when you agreed to go to dinner with me,” Derek said, ripping the package open and deftly slipping the condom on.

“Cocky,” Stiles groaned, fisting his hands in the bed sheets and biting his lip, enjoying the slight burn he felt from Derek’s fingers.

“Hopeful,” Derek admitted. “Ready? Because I can’t hold on much longer.”

Stiles blinked and looked up at Derek, shivering at the raw lust his saw in Derek’s eyes. “Yes,” he gasped. “Please, Derek … “

Derek gave Stiles and almost feral smile as he removed his fingers and began to slowly press forward, growling as he felt Stiles clench around him. “Tight.” His voice was gravely, gruff.

“Been a while,” Stiles moaned, a hand clutching one of Derek’s biceps as the other wrapped around his cock, stroking roughly. And it had been a while - a very weird, very drunken threesome with Danny and his friend Jackson a couple of years ago … Stiles had been almost celibate since then.

“Good,” Derek said possessively as he gave a quick thrust, watching Stiles’ eyes widen, hearing Stiles’ heart rate jump. “Okay?”

“Very okay,” Stiles whimpered. “Do that again.”

Derek happily obliged, thrusting slowly at first, then quicker and harder once he knew he wouldn’t hurt Stiles. He enjoyed the feeling of Stiles’ nails digging into his bicep, reached up and tugged playfully at Stiles’ hair.

Stiles went into sensation overload. His hand on his cock, Derek inside him, Derek’s hand in his hair … it didn’t take long before Stiles was coming, his come covering Derek’s stomach and splattering his chin.

Feeling Stiles clench around him sent Derek over the edge and he came with a howl, giving Stiles’ hair one last tug before collapsing on top of Stiles with a grunt. He nuzzled Stiles’ neck, licking at Stiles’ jaw and purring softly.

Stiles ran a hand up and down Derek’s back and gave a content hum. “We’re gonna stick together,” he mumbled.

“We’ll shower later,” Derek said, tugging on Stiles’ earlobe with his teeth. “Maybe after round two.”

“Round two?” Stiles said, his voice cracking just a little. “What … what about my double dark chocolate fudge brownies?”

Derek lifted his head and gave Stiles a grin. “Maybe shower, then brownies, then round two,” he said. “You’re going to need the energy.”

Stiles shivered. “I’m a ball of energy,” he whispered. “Are we planning on sleeping at all tonight?”

“Maybe,” Derek said, kissing Stiles gently. “Or maybe I’ll just tie you to the bed and have my way with you all night long.” He heard Stiles’ heart rate jump, saw Stiles’ face turn bright red and laughed. “Another kink we’ll have to play with.”

“We have time, right?” Stiles asked, uncertainty coloring his voice.

Derek smiled and nodded, resting his head on Stiles’ chest. “We have time.”


End file.
